CA2154116A1 - Derives 1-aryl-2-acetamidopentanone, destines a servir d'antagonistes du recepteur de tachykinine - Google Patents

Derives 1-aryl-2-acetamidopentanone, destines a servir d'antagonistes du recepteur de tachykinine

Info

Publication number: CA2154116A1
Authority: CA; Canada
Prior art keywords: phenyl; alkyl; compound; amino; alkylidenyl
Prior art date: 1994-07-22
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Abandoned

Application number

CA002154116A

Other languages

English (en)

Inventor

Philip Arthur Hipskind

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Eli Lilly and Co

Original Assignee

Eli Lilly and Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1994-07-22

Filing date

1995-07-18

Publication date

1996-01-23

1995-07-18 Application filed by Eli Lilly and Co filed Critical Eli Lilly and Co

1996-01-23 Publication of CA2154116A1 publication Critical patent/CA2154116A1/fr

Status Abandoned legal-status Critical Current

Links

239000002462 tachykinin receptor antagonist Substances 0.000 title description 12
150000001875 compounds Chemical class 0.000 claims abstract description 86
102000003141 Tachykinin Human genes 0.000 claims abstract description 13
108060008037 tachykinin Proteins 0.000 claims abstract description 13
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
230000002265 prevention Effects 0.000 claims abstract description 5
-1 phenoxy, phenylthio Chemical group 0.000 claims description 85
150000003839 salts Chemical class 0.000 claims description 29
239000004480 active ingredient Substances 0.000 claims description 25
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
125000003282 alkyl amino group Chemical group 0.000 claims description 12
239000001257 hydrogen Substances 0.000 claims description 10
229910052739 hydrogen Inorganic materials 0.000 claims description 10
125000004193 piperazinyl group Chemical group 0.000 claims description 10
125000003386 piperidinyl group Chemical group 0.000 claims description 10
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
125000005843 halogen group Chemical group 0.000 claims description 9
230000002829 reductive effect Effects 0.000 claims description 9
239000012453 solvate Substances 0.000 claims description 9
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 7
125000001624 naphthyl group Chemical group 0.000 claims description 7
239000000546 pharmaceutical excipient Substances 0.000 claims description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 6
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 5
230000003213 activating effect Effects 0.000 claims description 5
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 5
125000004076 pyridyl group Chemical group 0.000 claims description 5
125000005236 alkanoylamino group Chemical group 0.000 claims description 4
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
125000001041 indolyl group Chemical group 0.000 claims description 4
125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 4
125000002757 morpholinyl group Chemical group 0.000 claims description 4
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 4
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 3
125000001589 carboacyl group Chemical group 0.000 claims description 3
239000003795 chemical substances by application Substances 0.000 claims description 3
125000001309 chloro group Chemical group Cl* 0.000 claims description 3
239000003085 diluting agent Substances 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 3
125000001153 fluoro group Chemical group F* 0.000 claims description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
125000003705 anilinocarbonyl group Chemical group O=C([*])N([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 2
125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 claims description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 4
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 2
150000002431 hydrogen Chemical group 0.000 claims 2
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims 1
125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 1
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
125000000081 (C5-C8) cycloalkenyl group Chemical group 0.000 claims 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
238000000034 method Methods 0.000 abstract description 24
239000000203 mixture Substances 0.000 description 47
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
238000002360 preparation method Methods 0.000 description 31
238000006243 chemical reaction Methods 0.000 description 27
239000000243 solution Substances 0.000 description 23
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 22
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
239000000543 intermediate Substances 0.000 description 21
208000002193 Pain Diseases 0.000 description 19
125000000217 alkyl group Chemical group 0.000 description 19
208000035475 disorder Diseases 0.000 description 19
238000009472 formulation Methods 0.000 description 17
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 16
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
239000002585 base Substances 0.000 description 15
125000004432 carbon atom Chemical group C* 0.000 description 15
238000003786 synthesis reaction Methods 0.000 description 14
230000015572 biosynthetic process Effects 0.000 description 13
239000003814 drug Substances 0.000 description 13
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 12
238000007792 addition Methods 0.000 description 11
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235000019698 starch Nutrition 0.000 description 10
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
125000003545 alkoxy group Chemical group 0.000 description 9
108090000765 processed proteins & peptides Proteins 0.000 description 9
239000008107 starch Substances 0.000 description 9
239000003826 tablet Substances 0.000 description 9
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
239000002253 acid Substances 0.000 description 8
229940079593 drug Drugs 0.000 description 8
235000019359 magnesium stearate Nutrition 0.000 description 8
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
239000000651 prodrug Substances 0.000 description 8
229940002612 prodrug Drugs 0.000 description 8
239000002904 solvent Substances 0.000 description 8
LDWLIXZSDPXYDR-UHFFFAOYSA-N 3,5-bis(trifluoromethyl)benzaldehyde Chemical compound FC(F)(F)C1=CC(C=O)=CC(C(F)(F)F)=C1 LDWLIXZSDPXYDR-UHFFFAOYSA-N 0.000 description 7
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 7
102100024304 Protachykinin-1 Human genes 0.000 description 7
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
125000003277 amino group Chemical group 0.000 description 7
239000000047 product Substances 0.000 description 7
239000007787 solid Substances 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
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208000018522 Gastrointestinal disease Diseases 0.000 description 6
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000007983 Tris buffer Substances 0.000 description 6
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UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 6
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102000005962 receptors Human genes 0.000 description 6
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QDZOEBFLNHCSSF-PFFBOGFISA-N (2S)-2-[[(2R)-2-[[(2S)-1-[(2S)-6-amino-2-[[(2S)-1-[(2R)-2-amino-5-carbamimidamidopentanoyl]pyrrolidine-2-carbonyl]amino]hexanoyl]pyrrolidine-2-carbonyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-N-[(2R)-1-[[(2S)-1-[[(2R)-1-[[(2S)-1-[[(2S)-1-amino-4-methyl-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]pentanediamide Chemical compound C([C@@H](C(=O)N[C@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(N)=O)NC(=O)[C@@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](N)CCCNC(N)=N)C1=CC=CC=C1 QDZOEBFLNHCSSF-PFFBOGFISA-N 0.000 description 5
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KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
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DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
QJSOEMRUQKOCCR-UHFFFAOYSA-N tert-butyl n-[3-(1h-indol-3-yl)-1-[methoxy(methyl)amino]-1-oxopropan-2-yl]carbamate Chemical compound C1=CC=C2C(CC(C(=O)N(C)OC)NC(=O)OC(C)(C)C)=CNC2=C1 QJSOEMRUQKOCCR-UHFFFAOYSA-N 0.000 description 1
JSGUOHOUUIBULJ-UHFFFAOYSA-N tert-butyl n-[5-[3,5-bis(trifluoromethyl)phenyl]-1-(1h-indol-3-yl)-3-oxopentan-2-yl]carbamate Chemical compound C=1NC2=CC=CC=C2C=1CC(NC(=O)OC(C)(C)C)C(=O)CCC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 JSGUOHOUUIBULJ-UHFFFAOYSA-N 0.000 description 1
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235000010487 tragacanth Nutrition 0.000 description 1
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230000037317 transdermal delivery Effects 0.000 description 1
230000008733 trauma Effects 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 1
238000009827 uniform distribution Methods 0.000 description 1
125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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239000011995 wilkinson's catalyst Substances 0.000 description 1
UTODFRQBVUVYOB-UHFFFAOYSA-P wilkinson's catalyst Chemical compound [Cl-].C1=CC=CC=C1P(C=1C=CC=CC=1)(C=1C=CC=CC=1)[Rh+](P(C=1C=CC=CC=1)(C=1C=CC=CC=1)C=1C=CC=CC=1)P(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 UTODFRQBVUVYOB-UHFFFAOYSA-P 0.000 description 1
229940071104 xylenesulfonate Drugs 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
- C07D209/16—Tryptamines
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/16—Otologicals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Biomedical Technology (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Pain & Pain Management (AREA)
Psychiatry (AREA)
Pulmonology (AREA)
Heart & Thoracic Surgery (AREA)
Rheumatology (AREA)
Immunology (AREA)
Urology & Nephrology (AREA)
Cardiology (AREA)
Vascular Medicine (AREA)
Hospice & Palliative Care (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA002154116A 1994-07-22 1995-07-18 Derives 1-aryl-2-acetamidopentanone, destines a servir d'antagonistes du recepteur de tachykinine Abandoned CA2154116A1 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US27933094A	1994-07-22	1994-07-22
US08/279,330		1994-07-22

Publications (1)

Publication Number	Publication Date
CA2154116A1 true CA2154116A1 (fr)	1996-01-23

Family

ID=23068509

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002154116A Abandoned CA2154116A1 (fr)	1994-07-22	1995-07-18	Derives 1-aryl-2-acetamidopentanone, destines a servir d'antagonistes du recepteur de tachykinine

Country Status (3)

Country	Link
EP (1)	EP0699674A1 (fr)
JP (1)	JPH0859457A (fr)
CA (1)	CA2154116A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US7947458B1 (en)	1999-11-16	2011-05-24	Perinatal Diagnostics Limited	Placental human neurokinin B precursor

Families Citing this family (46)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5688960A (en) *	1995-05-02	1997-11-18	Schering Corporation	Substituted oximes, hydrazones and olefins useful as neurokinin antagonists
US5696267A (en) *	1995-05-02	1997-12-09	Schering Corporation	Substituted oximes, hydrazones and olefins as neurokinin antagonists
US5691362A (en) *	1996-06-05	1997-11-25	Schering-Plough Corporation	Substituted benzene-fused hetero- and carbocyclics as nuerokinin antagonists
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1995
- 1995-07-18 CA CA002154116A patent/CA2154116A1/fr not_active Abandoned
- 1995-07-20 EP EP95305084A patent/EP0699674A1/fr not_active Withdrawn
- 1995-07-21 JP JP7185524A patent/JPH0859457A/ja not_active Withdrawn

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EP0699674A1 (fr)	1996-03-06
JPH0859457A (ja)	1996-03-05

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Date	Code	Title	Description
2003-07-18	FZDE	Dead

Publication	Publication Date	Title
EP0699674A1 (fr)	1996-03-06	Dérivés de 1-aryl-2-acétylamidopentanone pour utilisation comme antagonistes de récepteurs de la tachykinine
CA2150992A1 (fr)	1995-12-11	Antagonistes cyclohexyliques du recepteur de la tachykinine
US5565568A (en)	1996-10-15	2-acylaminopropanamides as tachykinin receptor antagonists
CA2162786A1 (fr)	1996-05-23	Antagonistes heterocycliques des recepteurs des tachykinines
EP0729468B1 (fr)	2003-01-15	Antagonistes non peptidiques des recepteurs a la tachykinine
AU688072B2 (en)	1998-03-05	Heterocyclic tachykinin receptor antagonists
WO1994001402A1 (fr)	1994-01-20	Derives heterocycliques utiles comme antagonistes des recepteurs de tachykinine
US6358994B1 (en)	2002-03-19	2-acylaminopropanamines as tachykinin receptor antagonists
US6175013B1 (en)	2001-01-16	Imidazolinyl tachykinin receptor antagonists
US5563133A (en)	1996-10-08	Hexamethyleneiminyl tachykinin receptor antagonists
US6339094B1 (en)	2002-01-15	2-acylaminopropanamines as tachykinin receptor antagonists
US5607947A (en)	1997-03-04	Pyrrolidinyl tachykinin receptor antagonists
US6869957B1 (en)	2005-03-22	Non-peptide tachykinin receptor antagonists
AU721935B2 (en)	2000-07-20	Non-peptide tachykinin receptor antagonists
JP3657982B6 (ja)	2005-08-24	非ペプチド性タキキニン受容体拮抗物質
MXPA00001174A (en)	2001-05-17	2-acylaminopropanamines as tachykinin receptor antagonists
MXPA00001167A (en)	2001-05-17	2-acylaminopropanamines as tachykinin receptor antagonists
CZ2000375A3 (cs)	2000-07-12	Sloučeniny 2-acylaminopropanaminů jako antagonisté tachykininového receptoru

CA2154116A1 - Derives 1-aryl-2-acetamidopentanone, destines a servir d'antagonistes du recepteur de tachykinine - Google Patents

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